Novel indolizine compound, production process for novel indolizine compound, organic light-emitting device material having indolizine skeleton, and organic light-emitting device using these

ABSTRACT

An organic light-emitting device material is described, comprising at least one compound represented by formula (I) or a precursor thereof:  
                 
 
     wherein R 1  to R 7  each independently represents hydrogen atom, a halogen atom, a cyano group, a formyl group or a substituted or unsubstituted alkyl, alkenyl, alkynyl, aryl, heterocyclic, primary, secondary or tertiary amino, imino, alkoxy, aryloxy, alkylthio, arylthio, carbonamido, sulfonamido, carbamoyl, sulfamoyl, alkylcarbonyl, arylcarbonyl, alkylsulfonyl, arylsulfonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, urethane, ureido or carboxylic acid ester group, two or more groups selected from R 1  to R 7  may combine with each other to form an aliphatic carbon ring, an aromatic carbon ring, a non-aromatic heterocyclic ring or an aromatic heterocyclic ring and R 4  may further represent  
                 
 
     R 8  and R 9  each represents hydrogen atom, an alkyl group, an aryl group or a heterocyclic group, R 8  and R 9  may combine with each other to form a cyclic structure or may form a polymer compound having the structure represented by formula (I) in a part of the repeating unit thereof and R 1  or R 3  in the structure represented by formula (I) and  
                 
 
     may combine to form a trimer compound, and R represents hydrogen atom, an alkyl group, an aryl group or a heterocyclic group.

FIELD OF THE INVENTION

[0001] The present invention relates to a novel indolizine compound, amethod for producing a novel indolizine compound, an organiclight-emitting device material having an indolizine skeleton, and anorganic light-emitting device using these.

BACKGROUND OF THE INVENTION

[0002] At present, studies on and development of various displayelements are aggressively proceeding. In particular, organic ELlight-emitting devices can afford high luminance emission at a lowvoltage and is attracting an attention as a promising display device.For example, an EL device comprising an organic thin film formed bydepositing an organic compound is known (see, Applied Physics Letters,Vol. 51, page 913 (1987)). The organic EL device described in thispublication has a laminate structure comprising an electron-transportingmaterial and a hole-transporting material and is greatly improved in theemission properties as compared with conventional single-layer devices.

[0003] As concerns the hole-transporting material used in thelaminate-type device, triarylamine derivatives including TPD(N,N′-di-m-tolyl-N,N′-diphenylbezidine), and π-electron excess aromaticcompounds such as pyrrole, carbazole and thiophene, are known asexcellent hole-transporting materials. These π-electron excess aromaticcompounds are acknowledged to be effective not only as ahole-transporting material but also as an electron-transportingmaterial, a hole-injecting material or a light-emitting material.However, these compounds have high crystallinity and the organiclight-emitting devices using such a compound are known to have a problemin that the device performance is liable to greatly deteriorate duringstorage, particularly storage at a high temperature.

[0004] Triarylamine derivatives are low in the solubility in an organicsolvent and these compounds are not suitable for coating-type organic ELdevices.

[0005] As an electron-transporting material capable of taking the placeof the triarylamine derivatives, use of a nitrogen-containingheterocyclic compound such as carbazole derivative is being studied anda large number of cases have been reported on the technique of using alow molecular carbazole derivative or a polyvinyl carbazole as thehole-transporting material, for example, a compound described in OyoButsuri Gakkai Yuki Bunshi Bioelectronics Bunka-kai, Dai 6-kai Koshu-kaiYoko (1997) (Society of Applied Physics, Section of Organic MoleculesBioelectronics, 6th Lecture, Preprint), or the like.

[0006] However, as a result of investigations by the present inventorson the compounds such as carbazole derivative, these compounds have ahigh potential of ionization and have a problem in that an organic ELdevice capable of emitting light with high efficiency cannot beobtained.

[0007] As means for solving the problem of deterioration of the deviceperformance during storage, techniques of, in the case of triarylaminederivatives, introducing a condensed polycyclic aromatic group or usinga group of compounds improved in the symmetry property are disclosed inAppl. Phys. Lett., 56, 799 (1990), Polymer Preprints (ACS), 349 (1997),and the like. Similarly, investigations on nitrogen-containingheterocyclic compounds such as carbazole derivative, and techniques ofincreasing the molecular weight are disclosed in Appl. Phys. Lett., 63,2627 (1993).

[0008] The present inventors had found that indolizine compounds areeffective as the organic light-emitting device material and continuouslystudied on these compounds. Then, it was found that the indolizinecompounds have a problem, similarly to the heterocyclic compounds inseries, in that when a compound having a simple structure is used in theorganic light-emitting material, a sufficiently high performance cannotbe obtained.

[0009] Furthermore, in the case of using a known Chichibabin method forsynthesizing the indolizine compound, it was difficult to introduce asubstituent into various positions of the indolizine mother nucleus.Particularly, in introducing a substituent into the 5-position of theindolizine mother nucleus, when the substituent was introduced into apyridine ring of the starting material, the synthesis of indolizinemother nucleus encountered great steric hindrance and the mother nucleuswas difficult to form. When the substituent was attempted to introduceafter the ring formation, the substituent could not be easily introducedinto the 5-position because the 1-position and 3-position of theindolizine mother nucleus were extremely high in the reactivity with anelectrophilic reacting agent.

[0010] In recent years, examples of the metalation reaction at the5-position of the indolizine mother nucleus are reported in TetrahedronLett., 33 (31), 4433-4434 (1992). The present inventors thought that byutilizing this reaction, a substituent may be introduced into the5-position of the indolizine mother nucleus, and made extensiveinvestigations, as a result, it has been found that an indolizineboronic acid ester is effective.

[0011] The present invention has been accomplished as a result of theseextensive investigations.

SUMMARY OF THE INVENTION

[0012] A first object of the present invention is to develop aheterocyclic compound having a good hole-transporting ability andthereby develop an EL device material suitable for the manufacture ofhigh-luminance organic EL device.

[0013] A second object of the present invention is to develop ahole-transporting material capable of exhibiting good film-formingproperty at the fabrication of a device and imparting high stockstorability to the device and in turn develop an EL device materialhaving excellent stock storability.

[0014] A third object of the present invention is to develop an ELdevice material suitable for the manufacture of an organic EL devicecapable of emitting high-luminance light even in the case of acoating-type device.

[0015] A fourth object of the present invention is develop a novelindolizine compound and thereby developing an organic light-emittingmaterial suitable for the manufacture of an organic light-emittingdevice having high luminance and excellent durability.

[0016] A fifth object of the present invention is to find out a novelindolizine compound and a production process therefore and develop anorganic light-emitting material suitable for the manufacture of ahigh-luminance organic light-emitting device.

[0017] These objects of the present invention can be attained thefollowing indolizine compound, production process therefor, organiclight-emitting device material and organic light-emitting device.

[0018] 1) An organic light-emitting device material comprising at leastone compound represented by formula (I) or a precursor thereof:

[0019] wherein R₁ to R₇ each independently represents hydrogen atom, ahalogen atom, a cyano group, a formyl group, a substituted orunsubstituted alkyl group, a substituted or unsubstituted alkenyl group,a substituted or unsubstituted alkynyl group, a substituted orunsubstituted aryl group, a substituted or unsubstituted heterocyclicgroup, a substituted or unsubstituted primary amino group, a substitutedor unsubstituted secondary amino group, a substituted or unsubstitutedtertiary amino group, a substituted or unsubstituted imino group, asubstituted or unsubstituted alkoxy group, a substituted orunsubstituted aryloxy group, a substituted or unsubstituted alkylthiogroup, a substituted or unsubstituted arylthio group, a substituted orunsubstituted carbonamido group, a substituted or unsubstitutedsulfonamido group, a substituted or unsubstituted carbamoyl group, asubstituted or unsubstituted sulfamoyl group, a substituted orunsubstituted alkylcarbonyl group, a substituted or unsubstitutedarylcarbonyl group, a substituted or unsubstituted alkylsulfonyl group,a substituted or unsubstituted arylsulfonyl group, a substituted orunsubstituted alkoxycarbonyl group, a substituted or unsubstitutedaryloxycarbonyl group, a substituted or unsubstituted alkylcarbonyloxygroup, a substituted or unsubstituted arylcarbonyloxy group, asubstituted or unsubstituted urethane group, a substituted orunsubstituted ureido group or a substituted or unsubstituted carboxylicacid ester group, two or more groups selected from R₁ to R₇ may combinewith each other to form an aliphatic carbon ring, an aromatic carbonring, a non-aromatic heterocyclic ring or an aromatic heterocyclic ringand R₄ may further represent

[0020] R₈ and R₉ each represents hydrogen atom, an alkyl group, an arylgroup or a heterocyclic group, R₈ and R₉ may combine with each other toform a cyclic structure or may form a polymer compound having thestructure represented by formula (I) in a part of the repeating unitthereof and R₁ or R₃ in the structure represented by formula (I) and

[0021] may combine to form a trimer compound, and R represents hydrogenatom, an alkyl group, an aryl group or a heterocyclic group.

[0022] 2) The organic light-emitting device material as described in 1), which contains a polymer compound derived from a compound containing apolymerizable group in R₁ to R₇ of formula (I), a trimer compound formedresulting from the combining of R₁ or R₃ in formula (I) and

[0023] or a compound in which R₄ in formula (I) is

[0024] 3) A compound represented by the following formula

[0025] wherein R₂₁ to R₂₆ each independently represents a substituentselected from the group consisting of hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted alkenyl group,a substituted or unsubstituted alkynyl group, a substituted orunsubstituted aryl group, a substituted or unsubstituted heterocyclicgroup, a substituted or unsubstituted alkoxy group, a substituted orunsubstituted aryloxy group, a substituted or unsubstituted alkylthiogroup, a substituted or unsubstituted arylthio group, a substituted orunsubstituted alkylamino group, a substituted or unsubstituted arylaminogroup, a substituted or unsubstituted alkylcarbonyl group, a substitutedor unsubstituted arylcarbonyl group, a substituted or unsubstitutedalkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group,a substituted or unsubstituted alkoxycarbonyl group, a substituted orunsubstituted aryloxycarbonyl group, a substituted or unsubstitutedalkylcarbamoyl group, a substituted or unsubstituted arylcarbamoylgroup, a substituted or unsubstituted alkylsulfamoyl group, asubstituted or unsubstituted arylsulfamoyl group, a substituted orunsubstituted alkylcarbonyloxy group, a substituted or unsubstitutedarylcarbonyloxy group, a substituted or unsubstituted alkylcarbonamidogroup, a substituted or unsubstituted arylcarbonamido group, asubstituted or unsubstituted alkylsulfonamido group, a substituted orunsubstituted arylsulfonamido group, a substituted or unsubstitutedurethane group, a substituted or unsubstituted ureido group and asubstituted or unsubstituted carbonic acid ester group, the substituentsselected from R₂₁ to R₂₆ may combine with each other to form a cyclicstructure, R₂₇ and R₂₈ each represents hydrogen atom, an alkyl group, anaryl group or a heterocyclic group, and R₂₇ and R₂₈ may combine witheach other to form a cyclic structure.

[0026] 4) A method for synthesizing a compound represented by formula(IV), comprising metalating an indolizine derivative not having asubstituent at the 5-position and then reacting it with a boric acidester compound.

[0027] 5) A method for producing a compound represented by the followingformula (V), comprising coupling a compound represented by formula (IV)with a vinyl halide, aryl halide or heteroaryl halide compound using apalladium catalyst:

[0028] wherein R₂₀ represents an alkenyl group, an aryl group or aheteroaryl group, and R₂₁ to R₂₆ are the same as the substituentdescribed in formula (IV).

[0029] 6) An organic light-emitting device having at least one organiclight-emitting device material described in 1).

[0030] 7) The organic light-emitting device as described in 6), whereinat least one organic layer is formed by coating.

DETAILED DESCRIPTION OF THE INVENTION

[0031] The compound of the present invention is an indolizine derivativerepresented by formula (I). The compound of the present invention may beused as an organic light-emitting material in the form of the compoundrepresented by formula (I), or by using a precursor thereof in anorganic light-emitting device material, the compound of formula (I) maybe derived through a physical or chemical after-treatment during orafter the formation of the device.

[0032] The compound represented by formula (I) is described in detailbelow.

[0033] R₁ to R₇ each independently represents hydrogen atom, a halogenatom (e.g., fluorine, chlorine, bromine, iodine), a cyano group, aformyl group, a substituted or unsubstituted alkyl group (preferablyhaving from 1 to 30 carbon atoms, more preferably from 1 to 15 carbonatoms, e.g., methyl, t-butyl, cyclohexyl), a substituted orunsubstituted alkenyl group (preferably having from 2 to 30 carbonatoms, more preferably from 2 to 15 carbon atoms, e.g., vinyl,1-propenyl, 1-buten-2-yl, cyclohexen-1-yl), a substituted orunsubstituted alkynyl group (preferably having from 2 to 30 carbonatoms, more preferably from 2 to 15 carbon atoms, e.g., ethynyl,1-propynyl), a substituted or unsubstituted aryl group (preferablyhaving from 6 to 30 carbon atoms, more preferably from 6 to 15 carbonatoms, e.g., phenyl, tolyl, xylyl, naphthyl, biphenyl, pyrenyl), asubstituted or unsubstituted heterocyclic group (the heterocyclic ringis preferably a 5- or 6-membered ring and may be condensed with anotherring; examples of the heteroatom include nitrogen atom, oxygen atom andsulfur atom; the heterocyclic group preferably has from 2 to 30 carbonatoms, more preferably from 2 to 15 carbon atoms, e.g., pyridyl,piperidyl, oxazolyl, oxadiazolyl, tetrahydrofuryl, thienyl), asubstituted or unsubstituted primary, secondary or tertiary amino group(e.g. , amino, alkylamino, arylamino, dialkylamino, diarylamino,alkylarylamino, heterocyclic amino, bisheterocyclic amino; preferably atertiary amino group preferably having from 1 to 30 carbon atoms, morepreferably from 1 to 16 carbon atoms, e.g., dimethylamino,diphenylamino, phenylnaphthylamino), a substituted or unsubstitutedimino group (a group represented by —CR₃₁═NR₃₂ or —N═CR₃₃R₃₄, whereinR₃₁ to R₃₄ each is a group selected from hydrogen atom, an alkyl group,an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group,primary amino group, secondary amino group and tertiary amino group; theimino group preferably has from 1 to 30 carbon atoms, more preferablyfrom 1 to 15 carbon atoms) , a substituted or unsubstituted alkoxy group(preferably having from 1 to 30 carbon atoms, more preferably from 1 to15 carbon atoms, e.g., methoxy, ethoxy, cyclohexyloxy) , a substitutedor unsubstituted aryloxy group (preferably having from 6 to 30 carbonatoms, more preferably from 6 to 15 carbon atoms, e.g., phenoxy,1-naphthoxy, 4-phenylphenoxy), a substituted or unsubstituted alkylthiogroup (preferably having from 1 to 30 carbon atoms, more preferably from1 to 15 carbon atoms, e.g., methylthio, ethylthio, cyclohexylthio), asubstituted or unsubstituted arylthio group (preferably having 6 to 30carbon atoms, more preferably from 6 to 15 carbon atoms, e.g.,phenylthio, tolylthio), a substituted or unsubstituted carbonamido group(preferably having from 1 to 30 carbon atoms, more preferably from 1 to15 carbon atoms, e.g., acetamido, benzoylamido, N-methylbenzoylamido), asubstituted or unsubstituted sulfonamido group (preferably having from 1to 30 carbon atoms, more preferably from 1 to 15 carbon atoms, e.g.,methanesulfonamido, benzenesulfonamido, p-toluenesulfonamido), asubstituted or unsubstituted carbamoyl group (preferably having from 1to 30 carbon atoms, more preferably from 1 to 15 carbon atoms, e.g.,unsubstituted carbamoyl, methylcarbamoyl, dimethylcarbamoyl,phenylcarbamoyl, diphenylcarbamoyl, dioctylcarbamoyl), a substituted orunsubstituted sulfamoyl (preferably having from 1 to 30 carbon atoms,more preferably from 1 to 15 carbon atoms, e.g., unsubstitutedsulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenylsulfamoyl,diphenylsulfamoyl, dioctylsulfamoyl), a substituted or unsubstitutedalkylcarbonyl group (preferably having from 1 to 30 carbon atoms, morepreferably from 1 to 15 carbon atoms, e.g., acetyl, propionyl, butyroyl,lauroyl), a substituted or unsubstituted arylcarbonyl group (preferablyhaving from 6 to 30 carbon atoms, more preferably from 6 to 15 carbonatoms, e.g., benzoyl, naphthoyl), a substituted or unsubstitutedalkylsulfonyl group (preferably having from 1 to 30 carbon atoms, morepreferably from 1 to 15 carbon atoms, e.g., methanesulfonyl,ethanesulfonyl), a substituted or unsubstituted arylsulfonyl group(preferably having from 6 to 30 carbon atoms, more preferably from 6 to15 carbon atoms, e.g., benzenesulfonyl, p-toluenesulfonyl,1-naphthalenesulfonyl), a substituted or unsubstituted alkoxycarbonylgroup (preferably having from 1 to 30 carbon atoms, more preferably from1 to 15 carbon atoms, e.g., methoxycarbonyl, ethoxycarbonyl,butoxycarbonyl), a substituted or unsubstituted aryloxycarbonyl group(preferably having from 6 to 30 carbon atoms, more preferably from 6 to15 carbon atoms, e.g., phenoxycarbonyl, 1-naphthoxycarbonyl), asubstituted or unsubstituted alkylcarbonyloxy group (preferably havingfrom 1 to 30 carbon atoms, more preferably from 1 to 15 carbon atoms,e.g., acetoxy, propionyloxy, butyroyloxy), a substituted orunsubstituted arylcarbonyloxy group (preferably having from 6 to 30carbon atoms, more preferably from 6 to 15 carbon atoms, e.g.,benzoyloxy, 1-naphthoyloxy), a substituted or unsubstituted urethanegroup (preferably having from 1 to 30 carbon atoms, more preferably from1 to 15 carbon atoms, e.g., methoxycarbonamido, phenoxycarbonamido,methylaminocarbonamido), a substituted or unsubstituted ureido group(preferably having from 1 to 30 carbon atoms, more preferably from 1 to15 carbon atoms, e.g., methylaminocarbonamido, dimethylaminocarbonamido,diphenylaminocarbonamido) or a substituted or unsubstituted carbonicacid ester group (preferably having from 1 to 30 carbon atoms, morepreferably from 1 to 15 carbon atoms, e.g., methoxycarbonyloxy,phenoxycarbonyloxy).

[0034] Two or more groups selected from R₁ to R₇ may combine with eachother to form an aliphatic carbon ring, an aromatic carbon ring, anon-aromatic heterocyclic ring or an aromatic heterocyclic ring.

[0035] R₄ may represent

[0036] R₈ and R₉ each represents hydrogen atom, an alkyl group, an arylgroup or a heterocyclic group, R₈ and R₉ may combine with each other toform a cyclic structure.

[0037] Furthermore, a polymer compound having a structure represented byformula (I) in a part of the repeating unit may be formed. In this case,it may be possible to contain a polymerizable group such asethylenically unsaturated bond, or a polymerizable group capable ofcausing a condensation polymerization, such as carboxyl group, aminogroup or ester group, in R₁ to R₇ and form the polymer by thepolymerization of the group, or to form the polymer while allowing aprecursor of the compound represented by formula (I) to form theskeleton of the compound of formula (I).

[0038] In the structure represented by formula (I), R₁ or R₃ and

[0039] (wherein R represents hydrogen atom, an alkyl group, an arylgroup or a heterocyclic group) may combine to form a trimer compound.

[0040] The compound represented by formula (I) may be either a lowmolecule compound or a high molecular compound and the compound whichfinally works out to the structure capable of exerting the function canbe used as it is. The final structure may also be derived from aprecursor of the compound by using it in an organic light-emittingdevice and after or during the fabrication of a device, physically orchemically after-treating the device. In the case of a low molecularcompound, the molecular weight is preferably from 200 to 5,000, morepreferably from 300 to 2,000. In the case of a high molecular compound,the average molecular weight (Mw) is preferably from 2,000 to 1,000,000,more preferably from 5,000 to 100,000.

[0041] Among the above-described atoms and groups represented by R₁ toR₇, preferred are hydrogen atom, an alkyl group, an aryl group, aheterocyclic group and a tertiary amino group. In the case of a tertiaryamino group, the substituent is preferably an aryl group or aheteroaromatic group. In particular, a case where at least one of R₁ toR₃ is an aryl group or a heteroaromatic group is preferred.

[0042] The indolizine compound represented by formula (I) can besynthesized by a known method. A most commonly used method is asynthesis method of performing the ring formation by reacting2-alkylpyridine derivative and α -halogenoketone and treating theresulting quaternary ammonium salt in a basic aqueous solution. Ageneral synthesis scheme (see, L. F. Tietze & Th. Eicher (translated bySeiichi Takano and Kunio Ogasawara), Seimitsu Yuki Gosei-Jikken Manual,-Kaitei Dai 2-Han (Advanced Organic Synthesis, Manual for Experiments,2nd Ed.), pp. 344-345, Nankodo (1995)) is shown below and after that,specific examples of the compound of the present invention are setforth. Of course, the present invention is by no means limited thereto.

[0043] The compounds represented by formulae (II) and (III) aredescribed below

[0044] wherein R₁₁ to R₁₆ each independently represents a substituentselected from the group consisting of hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted alkenyl group,a substituted or unsubstituted alkenyl group, a substituted orunsubstituted alkynyl group, a substituted or unsubstituted aryl group,a substituted or unsubstituted heterocyclic group, a substituted orunsubstituted alkoxy group, a substituted or unsubstituted aryloxygroup, a substituted or unsubstituted alkylthio group, a substituted orunsubstituted arylthio group, a substituted or unsubstituted alkylaminogroup, a substituted or unsubstituted arylamino group, a substituted orunsubstituted alkylcarbonyl group, a substituted or unsubstitutedarylcarbonyl group, a substituted or unsubstituted alkylsulfonyl group,a substituted or unsubstituted arylsulfonyl group, a substituted orunsubstituted alkoxycarbonyl group, a substituted or unsubstitutedaryloxycarbonyl group, a substituted or unsubstituted carbamoyl group, asubstituted or unsubstituted alkylcarbamoyl group, a substituted orunsubstituted arylcarbamoyl group, a substituted or unsubstitutedsulfamoyl group, a substituted or unsubstituted alkylsulfamoyl group, asubstituted or unsubstituted arylsulfamoyl group, a substituted orunsubstituted alkylcarbonyloxy group, a substituted or unsubstitutedarylcarbonyloxy group, a substituted or unsubstituted alkylcarbonamidogroup, a substituted or unsubstituted arylcarbonamido group, asubstituted or unsubstituted alkylsulfonamido group, a substituted orunsubstituted arylsulfonamido group, a substituted or unsubstitutedurethane group, a substituted or unsubstituted ureido group and asubstituted or unsubstituted carbonic acid ester group, the substituentsselected from R₁₁ to R₁₆ may combine with each other to form a cyclicstructure, and R represents hydrogen atom, an alkyl group, an aryl groupor a heterocyclic group.

[0045] The compounds represented by formulae (II) and (III) are atrisheteroarylmethane where three indolizine rings are bonded to amethine group in the moiety at the 1- or 3-position.

[0046] R₁₁ to R₁₆, which are substituents common in formulae (II) and(III), each independently represents hydrogen atom, a substituted orunsubstituted alkyl group (preferably having from 1 to 20 carbon atoms,e.g., methyl, ethyl, n-propyl, i-propyl, n-butyl, t-butyl, octyl,dodecyl, benzyl, cyclopropyl, cyclohexyl), a substituted orunsubstituted alkenyl group (preferably having from 2 to 20 carbonatoms, e.g., ethynyl, propenyl, butenyl), a substituted or unsubstitutedalkynyl group (preferably having from 2 to 20 carbon atoms, e.g.,ethynyl, propynyl, butynyl), a substituted or unsubstituted aryl group(preferably having from 6 to 20 carbon atoms, e.g., phenyl, 1-naphthyl,2-naphthyl, 4-methoxyphenyl, 3-methylphenyl, 9-phenanthryl, 9-anthryl,1-pyrenyl), a substituted or unsubstituted heterocyclic group(preferably having from 1 to 20 carbon atoms; preferred examples of theheterocyclic ring include a 5-membered aromatic ring such as pyrrole,thiophene, furan, imidazole, pyrazole, thiazole, oxazole, triazole,oxadiazole and thiadiazole, a condensed ring thereof, a 6-membered ringsuch as pyridine, pyridazine, pyrimidine, pyrazine and triazine, and acondensed ring thereof; the heterocyclic ring may also be a non-aromaticheterocyclic ring represented by piperidine, tetrahydrofuran andtetrahydrothiophene), a substituted or unsubstituted alkylamino group(e.g., methylamino, dimethylamino, diethylamino, morpholino,pyrrolidino, piperidino, the alkylamino group is preferably a tertiaryamino group having from 1 to 30 carbon atoms, more preferably from 1 to16 carbon atoms), a substituted or unsubstituted arylamino group(including a heteroarylamino group; e.g. , anilino, diphenylamino,1-naphthylphenylamino, 2-naphthylphenylamino, N-ethylphenylamino; thearylamino group is preferably a tertiary amino group having from 6 to 30carbon atoms, more preferably from 6 to 16 carbon atoms), a substitutedor unsubstituted alkoxy group (preferably having from 1 to 30 carbonatoms, more preferably from 1 to 15 carbon atoms, e.g., methoxy, ethoxy,cyclohexyloxy), a substituted or unsubstituted aryloxy group (includinga heteroaryloxy group; preferably having from 6 to 30 carbon atoms, morepreferably from 6 to 15 carbon atoms, e.g., phenoxy, 1-naphthoxy,4-phenylphenoxy), a substituted or unsubstituted alkylthio group(preferably having from 1 to 30 carbon atoms, more preferably from 1 to15 carbon atoms, e.g., methylthio, ethylthio, cyclohexylthio), asubstituted or unsubstituted arylthio group (including a heteroarylthiogroup; preferably having 6 to 30 carbon atoms, more preferably from 6 to15 carbon atoms, e.g., phenylthio, tolylthio), a substituted orunsubstituted alkylcarbonyl group (preferably having from 1 to 30 carbonatoms, more preferably from 1 to 15 carbon atoms, e.g., acetyl,propionyl, butyroyl, lauroyl), a substituted or unsubstitutedarylcarbonyl group (including a heteroarylcarbonyl group; preferablyhaving from 6 to 30 carbon atoms, more preferably from 6 to 15 carbonatoms, e.g., benzoyl, naphthoyl), a substituted or unsubstitutedalkylsulfonyl group (preferably having from 1 to 30 carbon atoms, morepreferably from 1 to 15 carbon atoms, e.g., methanesulfonyl,ethanesulfonyl), a substituted or unsubstituted arylsulfonyl group(including a heteroarylsulfonyl group; preferably having from 6 to 30carbon atoms, more preferably from 6 to 15 carbon atoms, e.g.,benzenesulfonyl, p-toluenesulfonyl, 1-naphthalene-sulfonyl), asubstituted or unsubstituted alkoxycarbonyl group (preferably havingfrom 1 to 30 carbon atoms, more preferably from 1 to 15 carbon atoms,e.g., methoxycarbonyl, ethoxycarbonyl, butoxycarbonyl), a substituted orunsubstituted aryloxycarbonyl group (including a heteroaryloxycarbonylgroup; preferably having from 6 to 30 carbon atoms, more preferably from6 to 15 carbon atoms, e.g., phenoxycarbonyl, 1-naphthoxycarbonyl), asubstituted or unsubstituted alkylcarbonamido group (preferably havingfrom 1 to 30 carbon atoms, more preferably from 1 to 15 carbon atoms,e.g., acetamido, propionylamido, butyroylamido), a substituted orunsubstituted arylcarbonamido group (including a heteroarylcarbonamidogroup; preferably having from 6 to 30 carbon atoms, more preferably from6 to 15 carbon atoms, e.g., benzoylamido, N-methylbenzoylamido) asubstituted or unsubstituted alkylsulfonamido group (preferably havingfrom 1 to 30, more preferably from 1 to 15 carbon atoms, e.g.,methanesulfonamido, ethanesulfonamido, butanesulfonamido), a substitutedor unsubstituted arylsulfonamido group (including aheteroarylsulfonamido group; preferably having from 6 to 30 carbonatoms, more preferably from 6 to 15 carbon atoms, e.g.,benzenesulfonamido, p-toluenesulfonamido, 1-naphthalenesulfonamido), asubstituted or unsubstituted carbamoyl group, a substituted orunsubstituted alkylcarbamoyl group (preferably having from 1 to 30carbon atoms, more preferably from 1 to 15 carbon atoms, e.g.,methylcarbamoyl, dimethylcarbamoyl, diethylcarbamoyl, dioctylcarbamoyl),a substituted or unsubstituted arylcarbamoyl group (including aheteroarylcarbamoyl group; preferably having from 6 to 30 carbon atoms,more preferably from 6 to 15 carbon atoms, e.g., phenylcarbamoyl,diphenylcarbamoyl, methylphenylcarbamoyl), a substituted orunsubstituted sulfamoyl group, a substituted or unsubstitutedalkylsulfamoyl group (preferably having from 1 to 30 carbon atoms, morepreferably from 1 to 15 carbon atoms, e.g., methylsulfamoyl,dimethylsulfamoyl, diethylsulfamoyl, dioctylsulfamoyl), a substituted orunsubstituted arylsulfamoyl group (including a heteroarylsulfamoylgroup; preferably having from 6 to 30 carbon atoms, more preferably from6 to 15 carbon atoms, e.g., phenylsulfamoyl, diphenylsulfamoyl,methylphenylsulfamoyl), a substituted or unsubstituted alkylcarbonyloxygroup (preferably having from 1 to 30 carbon atoms, more preferably from1 to 15 carbon atoms, e.g., acetoxy, propionyloxy, butyroyloxy), asubstituted or unsubstituted arylcarbonyloxy group (including aheteroarylcarbonyloxy group; preferably having from 6 to 30 carbonatoms, more preferably from 6 to 15 carbon atoms, e.g., benzoyloxy,1-naphthoyloxy), a substituted or unsubstituted urethane group(preferably having from 1 to 30 carbon atoms, more preferably from 1 to15 carbon atoms, e.g., methoxycarbonamido, phenoxycarbonamido,methylaminocarbonamido), a substituted or unsubstituted ureido group(preferably having from 1 to 30 carbon atoms, more preferably from 1 to15 carbon atoms, e.g., methylaminocarbonamido, dimethylaminocarbonamido,diphenylaminocarbonamido) or a substituted or unsubstituted carbonicacid ester group (preferably having from 1 to 30 carbon atoms, morepreferably from 1 to 15 carbon atoms, e.g., methoxycarbonyloxy,phenoxycarbonyloxy).

[0047] R represents hydrogen atom, an alkyl group (preferably havingfrom 1 to 20 carbon atoms, e.g., methyl, ethyl, n-propyl, i-propyl,n-butyl, t-butyl, octyl, dodecyl, benzyl, cyclopropyl, cyclohexyl), anaryl group (preferably having from 6 to 20 carbon atoms, e.g., phenyl,1-naphthyl, 2-naphthyl, 4-methoxyphenyl, 3-methylphenyl, 9-phenanthryl,9-anthryl, 1-pyrenyl) or a heterocyclic group (preferably having from 1to 20 carbon atoms; preferred examples of the heterocyclic ring includea 5-membered aromatic ring such as pyrrole, thiophene, furan, imidazole,pyrazole, thiazole, oxazole, triazole, oxadiazole and thiazole, acondensed ring thereof, a 6-membered aromatic ring such as pyridine,pyridazine, pyrimidine, pyrazine and triazine, and a condensed ringthereof; the heterocyclic ring may also be a non-aromatic heterocyclicring represented by piperidine, tetrahydrofuran andtetrahydrothiophene). R is preferably hydrogen atom.

[0048] Out of R₁₁ to R₁₆, at least one of R₁₁ to R₁₄ is preferablysubstituted by a substituent except for hydrogen atom, or at least oneof R₁₅ and R₁₆ is preferably substituted by a substituent except forhydrogen atom, and the substituent is preferably selected from the groupconsisting of an alkyl group, an aryl group, an alkenyl group, analkynyl group and a heterocyclic group. The compound is more preferablya compound where at least one of R₁₅ and R₁₆ has two or more benzenerings or at least one substituent selected from a condensedpolycycloaromatic hydrocarbon group and a heteroaromacyclic group.

[0049] The compounds represented by formulae (II) and (III) each may bea compound which itself finally works out to a structure capable ofexerting the function. Alternatively, the final structure may be derivedfrom a precursor of the compound by using it in an organic EL device andafter or during the fabrication of the device, physically or chemicallyafter-treating the device. The compounds represented by formulae (II)and (III) each preferably has a molecular weight of 200 to 5,000, morepreferably from 300 to 2,000.

[0050] The compounds represented by formulae (II) and (III) can besynthesized by a known method. The indolizine compound can besynthesized by the Chichibabin method (a ring formation reaction throughproduction of a pyridinium salt from a picoline derivative and anα-halocarbonyl compound and subsequent treatment with a basic aqueoussolution). The compounds represented by formulae (II) and (III) each canbe derived from this indolizine compound by treating the compound inanhydrous methanol in the presence of a sulfuric acid catalyst using anortho-ester such as ethyl orthoformate (a method described in Chem.Ber., 120, 239-242 (1987)). A general synthesis scheme is disclosedbelow and after that, specific examples of the compounds of the presentinvention are set forth. The present invention is not limited to thosespecific examples.

[Synthesis of Compound B-HT-1] (Synthesis of Compound A)

[0051] To 1,200 ml of toluene, 169.2 g (1.0 mol) of 2-benzylpyridine wasadded while stirring to form a uniform solution. The temperature of thissolution was elevated to 80° C. and thereto, 199 g (1.0 mol) of phenacylbromide was gradually added while stirring. The stirring was continued,as a result, crystals were precipitated. The temperature was elevated tothe reflux conditions and the reaction was continued for another 1 hourwhile stirring. After cooling, the precipitated crystals were separatedby filtration and then washed with toluene and subsequently withn-hexane to obtain 327 g of crystals of Compound A.

(Synthesis of Compound B)

[0052] Into 3,000 ml-volume three-neck flask, 295 g (0.8 mol) ofCompound A was charged and after adding 1,000 ml of water, the compoundwas dissolved while stirring. A nitrogen stream was passed therethrough,84 g (1.0 mol) sodium hydrogencarbonate was added thereto, and the innertemperature was elevated up to 85° C. in a steam bath while stirring.The stirring was continued, as a result, vigorous bubbling took placeand pale yellow crystals were precipitated. The reaction was continuedfor another 1 hour and after cooling to room temperature, theprecipitated crystals were separated by filtration. These crystals wererecrystallized from a acetonitrile-water mixed solvent to obtain 186 gof crystals of Compound B.

(Synthesis of Compound B-HT-1)

[0053] To 300 ml of dehydrated methanol for organic synthesis, 67.3 g(0.25 mol) of Compound B was added and stirred. Thereto, 11.8 g (0.08mol) of ethyl orthoformate and 1 ml of concentrated sulfuric acid wereadded and reacted under reflux for 2 hours. At first, the color of thesolution was turned to deep blue green and after a while, white crystalswere precipitated. After the completion of reaction, the crystals stillin the hot state were filtered and the obtained crystals wererecrystallized from a tetrahydrofuran-methanol mixed solvent to obtain48 g of crystals of Compound B-HT-1.

[0054] The compound represented by formula (IV) is described below. Thecompound represented by formula (IV) is a compound which can begenerically called an indolizine boronic acid derivative. The compoundof the present invention is characterized in that the substitution sitethereof is the 5-position of the indolizine ring. In formula (IV) , thesubstituents R₂₁ to R₂₆ each represents a substituent selected from thegroup consisting of hydrogen atom, a substituted or unsubstituted alkylgroup, a substituted or unsubstituted alkenyl group, a substituted orunsubstituted alkynyl group, a substituted or unsubstituted aryl group,a substituted or unsubstituted heterocyclic group, a substituted orunsubstituted alkoxy group, a substituted or unsubstituted aryloxygroup, a substituted or unsubstituted heteroaryloxy group, substitutedor unsubstituted alkylthio group, a substituted or unsubstitutedarylthio group, a substituted or unsubstituted heteroarylthio group, asubstituted or unsubstituted alkylamino group, a substituted orunsubstituted arylamino group, a substituted or unsubstitutedheteroarylamino group, a substituted or unsubstituted alkylcarbonylgroup, a substituted or unsubstituted arylcarbonyl group, a substitutedor unsubstituted heteroarylcarbonyl group, a substituted orunsubstituted alkylsulfonyl group, a substituted or unsubstitutedarylsulfonyl group, a substituted or unsubstituted heteroarylsulfonylgroup, a substituted or unsubstituted alkoxycarbonyl group, asubstituted or unsubstituted aryloxycarbonyl group, a substituted orunsubstituted heteroaryloxycarbonyl group, a substituted orunsubstituted alkylcarbamoyl group, a substituted or unsubstitutedarylcarbamoyl group, a substituted or unsubstituted heteroarylcarbamoylgroup, a substituted or unsubstituted alkylsulfamoyl group, asubstituted or unsubstituted arylsulfamoyl group, a substituted orunsubstituted heteroarylsulfamoyl group, a substituted or unsubstitutedalkylcarbonyloxy group, a substituted or unsubstituted arylcarbonyloxygroup, a substituted or unsubstituted heteroarylcarbonyloxy group, asubstituted or unsubstituted alkylcarbonamido group, a substituted orunsubstituted arylcarbonamido group, a substituted or unsubstitutedheteroarylcarbonamido group, a substituted or unsubstitutedalkylsulfonamido group, a substituted or unsubstituted arylsulfonamidogroup, a substituted or unsubstituted heteroarylsulfonamido group, asubstituted or unsubstituted urethane group, a substituted orunsubstituted ureido group and a substituted or unsubstituted carbonicacid ester group. In the present invention, the compound represented byformula (IV) is obtained through a metalation reaction, therefore, thesubstituents R₂₁ to R₂₆ are preferably not substituted by hydrogen atomwhich may be metalated. For example, in all substituents, a dissociativeproton (e.g., —OH, —NH, —SH) substituted to a hetero atom is preferablynot present. In the case of an alkyl group, the carbon atom bonded tothe indolizine ring is preferably not substituted by hydrogen atom. Thealkenyl group, aryl group or heteroaryl group is preferably notsubstituted by a halogen atom such as bromo group or iodo group.Examples of the substituent except for hydrogen atom, which can bepreferably substituted to R₂₁ to R₂₆, include a t-butyl group, a phenylgroup and a naphthyl group. The substituents selected from R₂₁ to R₂₆can combine with each other to form a cyclic structure.

[0055] R₂₇ and R₂₈ each represents hydrogen atom, an alkyl group, anaryl group or a heterocyclic group, preferably hydrogen atom or an alkylgroup. R₂₇ and R₂₈ may combine with each other to form a cyclicstructure.

[0056] In the present invention, the compound represented by formula(IV) is synthesized by a method of metalating an indolizine compound andthen reacting the metalated compound with a boric acid ester compound.The term “metalation” as used herein means a reaction where anindolizine compound is treated in an ether-base solvent underlow-temperature conditions using an alkali metal compound, an alkalineearth metal compound, metal zinc or an alkyl- or aryl-substitutionproduct thereof to displace the hydrogen atom at the 5-position of theindolizine ring by a metal atom. Among alkali metal compounds, alkalineearth metal compounds and the like, preferred are lithium, sodium,potassium, calcium, magnesium and zinc, more preferred are lithium andmagnesium. In the metalation reaction, a metal may be used as it is butin the case of lithium and the like, an exchange reaction with acommercially available alkyl-substitution product is preferably used inview of safety and operability. The boronic acid ester is preferably atrialkoxyborane derivative.

[0057] The metalation reaction and the reaction between the metalatedindolizine compound and a boronic ester compound each is preferablyperformed at 20° C. or less, more preferably 0° C. or less, still morepreferably −20° C. or less. The reaction time is preferably from 5minutes to 10 hours, more preferably from 10 minutes to 5 hours, stillmore preferably from 30 minutes to 2 hours. The compound used in themetalation reaction and the boric acid ester compound each is preferablyused in an amount of 0.1 to 100 molar equivalent, more preferably from0.5 to 10 molar equivalent, still more preferably from 1 to 5 molarequivalent, to the indolizine compound as an objective of the reaction.

[0058] The compound (V) is described below. The compound represented byformula (V) is a compound in which an alkenyl group, an aryl group or aheteroaryl group is substituted at the 5-position of the indolizinering. This compound is synthesized by the reaction of the compoundrepresented by formula (IV) with a vinyl halide, aryl halide orheteroaryl halide compound. This reaction can be performed by applying aSuzuki coupling reaction known in the field of organic synthesischemistry (see, Katsuyuki Ogura, Yuki Jinmei Han'no (Named Reactions inOrganic Chemistry), Asakura Shoten (1997)). In practice, the reaction ispreferably performed using a palladium catalyst and a phosphinederivative as a phosphorus-base compound. In this reaction, the reactiontemperature is preferably from 50 to 250° C., more preferably from 100to 200° C. The vinyl halide or the like is preferably used in an amountof 0.5 to 5 molar equivalent to the compound represented by formula(IV).

[0059] R₂₀ represents an alkenyl group (preferably having from 2 to 20carbon atoms, e.g., 2-phenylvinyl), an aryl group (preferably havingfrom 6 to 20 carbon atoms, e.g., phenyl, 1-naphthyl, 2-naphthyl,4-methoxyphenyl, 3-methylphenyl, 9-phenanthryl, 9-anthryl, 1-pyrenyl) ora heteroaryl group (preferably having from 1 to 20 carbon atoms;preferred examples of the heterocyclic ring include a 5-memberedaromatic ring such as pyrrole, thiophene, furan, imidazole, pyrazole,thiazole, oxazole, triazole, oxadiazole and thiadiazole, a condensedring thereof, a 6-membered aromatic ring such as pyridine, pyridazine,pyrimidine, pyrazine and triazine, and a condensed ring thereof).

[0060] In the present invention, the compound represented by formula (V)is used as the organic light-emitting device material. In the case ofusing the compound represented by formula (V) as the organiclight-emitting device material, when a low molecular compound is used,the molecular weight thereof is preferably from 200 to 5,000, morepreferably from 300 to 2,000. A polymer compound starting from thecompound represented by formula (V) may also be used. In this case, thepolymer may be used by introducing a polymerizable group such as anethylenically unsaturated bond or a polymerizable group capable ofbringing out polycondensation, such as carboxyl group, amino group andester group, into R₂₁ to R₂₆ or R₂₀ and causing polymerization of thegroup. Also, the polymer may be formed while allowing a precursor of thecompound represented by formula (V) to form the skeleton of the compoundrepresented by formula (V). When a high molecular compound is used, theaverage molecular weight (Mw) is preferably from 2,000 to 1,000,000,more preferably from 5,000 to 100,000.

[0061] The basic skeleton of the indolizine compound included in formula(IV) can be synthesized by a known method. The indolizine compound canbe synthesized by the Chichibabin method (a ring formation reactionthrough production of a pyridinium salt from a picoline derivative andan α -halocarbonyl compound and subsequent treatment with a basicaqueous solution). The compound represented by formula (IV) issynthesized by reacting the metalated indolizine compound with a boricacid ester. Through a Suzuki coupling reaction between this compound anda vinyl halide, aryl halide or heteroaryl halide compound, the compoundof formula (V) can be synthesized.

[0062] A general synthesis scheme is disclosed below and after that,specific examples of the compounds of the present invention are setforth. Of course, the present invention is not limited to these specificexamples.

Synthesis Route of Compound INB-1 of Formula (IV)

[0063]

Synthesis Route of Compound C-HT-10 of Formula (V)

[0064]

Examples of Compound Represented by Formula (IV)

[0065]

Examples of Compound Represented by Formula (V)

[0066]

[0067] The light-emitting device containing the compound of the presentinvention is described below. The method for forming the organic layerof the light-emitting device containing the compound of the presentinvention is not particularly limited but a resistance heatingevaporation, electron beam, sputtering, molecular lamination, coating,printing or inkjet method is used. In view of the properties andproduction, a resistance heating evaporation method and a coating methodare preferred.

[0068] The light-emitting device of the present invention is a devicefabricated by forming a light-emitting layer or a plurality of organiccompound thin films containing a light-emitting layer between a pair ofelectrodes of anode and cathode. In addition to the light-emittinglayer, a hole-injecting layer, a hole-transporting layer, anelectron-injecting layer, an electron-transporting layer, a protectivelayer and the like may be provided. These layers each may have afunction other than the function intended. For forming each layer,various materials may be used.

[0069] The anode feeds holes to the hole-injecting layer, thehole-transporting layer or the light-emitting layer, and a metal, analloy, a metal oxide, an electrically conducting compound or a mixturethereof may be used therefor. A material having a work function of 4 eVor more is preferred. Specific examples thereof include electricallyconducting metal oxides such as tin oxide, zinc oxide, indium oxide andindium tin oxide (ITO), metals such as gold, silver, chromium andnickel, a mixture or laminate of the metal with the electricallyconducting metal oxide, inorganic electrically conducting materials suchas copper iodide and copper sulfide, organic electrically conductingmaterials such as polyaniline, polythiophene and polypyrrole, and alaminate of the material with ITO. Among these, electrically conductingmetal oxides are preferred and in view of productivity, high electricalconductivity and transparency, ITO is more preferred. The thickness ofthe anode may be freely selected depending on the material used,however, it is usually in the range of preferably from 10 nm to 5 μm,more preferably from 50 nm to 1 μm, still more preferably from 100 to500 nm.

[0070] The anode is usually a layer formed on a soda lime glass, analkali-free glass or a transparent resin substrate. In the case of usinga glass, the constructive material therefor is preferably an alkali-freeglass so as to reduce the ion dissolved out from the glass. In the caseof using a soda lime glass, the glass is preferably subjected to barriercoating with silica or the like. The thickness of the substrate is notparticularly limited as long as it is sufficiently large to maintain themechanical strength, however, in the case of using a glass, thethickness is usually 0.2 mm or more, preferably 0.7 mm or more. Theanode may be prepared by various methods according to the material usedand for example, in the case of ITO, the layer is formed by an electronbeam method, a sputtering method, a resistance heating evaporationmethod, a chemical reaction method (sol-gel process) or a method ofcoating an indium tin oxide dispersion. By subjecting the anode torinsing or other treatments, the device driving voltage can be loweredor the light-emission efficiency can be increased. For example, in thecase of ITO, a UV-ozone treatment and a plasma treatment are effective.

[0071] The cathode feeds electrons to the electron-injecting layer, theelectron-transporting layer or the light-emitting layer and is selectedby taking account of the adhesion to the layer adjacent to the negativeelectrode, such as an electron-injecting layer, an electron-transportinglayer and a light-emitting layer, the ionization potential and thestability. As the material for the cathode, a metal, an alloy, a metalhalide, a metal oxide, an electrically conducting compound or a mixturethereof may be used and specific examples thereof include an alkalimetal (e.g., Li, Na, K, Cs) and fluoride and oxide thereof, an alkalineearth metal (e.g., Mg, Ca) and fluoride and oxide thereof, gold, silver,lead, aluminum, a sodium-potassium alloy or mixed metal, alithium-aluminum alloy or mixed metal, a magnesium-silver alloy or mixedmetal, and a rare earth metal such as indium and ytterbium. Among these,preferred are materials having a work function of 4 eV or less, morepreferred are aluminum, a lithium-aluminum alloy or mixed metal, and amagnesium-silver alloy or mixed metal. The cathode may have not only asingle layer structure of the above-described compound or a mixture ofthose compounds but also a laminate structure containing theabove-described compound or a mixture of those compounds. The thicknessof the cathode may be freely selected depending on the material used,however, it is usually in the range of preferably from 10 nm to 5 μm,more preferably from 50 nm to 1 μm, still more preferably from 100 nm to1 μm. The cathode may be manufactured by an electron beam method, asputtering method, a resistance heating evaporation method or a coatingmethod, and a sole metal may be deposited or two or more components maybe simultaneously deposited. Furthermore, a plurality of metals may beco-deposited to form an alloy electrode, or an alloy previously preparedmay be deposited. The anode and the cathode each preferably has a lowsheet resistance of hundreds of Ω/□ or less.

[0072] The material for the light-emitting layer may be any as long asit can form a layer having a function of injecting holes from the anode,hole-injecting layer or hole-transporting layer and at the same timeinjecting electrons from the cathode, electron-injecting layer orelectron-transporting layer upon application of an electric field, afunction of transferring charges injected, or a function of offering achance to the hole and the electron to recombine and emit light. Thelight-emitting layer is preferably a layer containing an amine compoundof the present invention but other light-emitting materials may also beused. Examples thereof include various metal complexes andorthometalated complexes including metal complexes and rare earthcomplexes of benzoxazole derivative, benzimidazole derivative,benzothiazole derivative, styrylbenzene derivative, polyphenylderivative, diphenylbutadiene derivative, tetraphenylbutadienederivative, naphthalimide derivative, coumarin derivative, perylenederivative, perynone derivative, oxadiazole derivative, aldazinederivative, pyralidine derivative, cyclopentadiene derivative,bisstyrylanthracene derivative, quinacridone derivative, pyrrolopyridinederivative, thiazolopyridine derivative, cyclopentadiene derivative,styrylamine derivative, aromatic dimethylidyne compound and 8-quinolinolderivative, and polymer compounds such as polythiophene, polyphenyleneand polyphenylenevinylene. The thickness of the light-emitting layer isnot particularly limited, however, it is usually in the range ofpreferably from 1 nm to 5 μm, more preferably from 5 nm to 1 μm, stillmore preferably from 10 to 500 nm.

[0073] The method for forming the light-emitting layer is notparticularly limited and a resistance heating evaporation method, anelectron beam method, a sputtering method, a molecular laminationmethod, a coating method (e.g., spin coating, casting, dip coating), anLB method, a printing method or an inkjet method may be used. Amongthese, preferred are a resistance heating evaporation method and acoating method.

[0074] The material for the hole-injecting layer and thehole-transporting layer may be any as long as it has any one of afunction of injecting holes from the anode, a function of transportingholes and a function of blocking electrons injected from the cathode.Specific examples thereof include electrically conducting high molecularoligomers such as carbazole derivative, triazole derivative, oxazolederivative, oxadiazole derivative, imidazole derivative, polyarylalkanederivative, pyrazoline derivative, pyrazolone derivative,phenylenediamine derivative, arylamine derivative, amino-substitutedchalcone derivative, styrylanthracene derivative, fluorenone derivative,hydrazone derivative, stilbene derivative, silazane derivative, aromatictertiary amine compound, styrylamine compound, aromaticdimethylidyne-base compound, porphyrin-base compound, polysilane-basecompound, poly(N-vinylcarbazole) derivative, aniline-base copolymer,thiophene oligomer and polythiophene. In the present invention, thecompound represented by formula (I), (II), (III), (IV) or (V) is used tothis purpose. The hole-injecting layer and the hole-transporting are notparticularly limited on the thickness, however, the thickness is usuallyin the range of preferably from 1 nm to 5 μm, more preferably from 5 nmto 1 μm, still more preferably from 10 to 500 nm. The hole-injectinglayer and the hole-transporting layer each may have a single layerstructure comprising one or more of the above-described materials or mayhave a multi-layer structure comprising a plurality of layers which arethe same or different in the composition.

[0075] The hole-injecting layer and the hole-transporting layer each isformed by a vacuum evaporation method, an LB method, an inkjet method, amethod of dissolving or dispersing the above-described hole-injectingand transporting agent in a solvent and coating the solution ordispersion (e.g., spin coating, casting, dip coating) or a printingmethod. In the case of the coating method, the material can be dissolvedor dispersed together with a resin component. Examples of the resincomponent include polyvinyl chloride, polycarbonate, polystyrene,polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone,polyphenylene oxide, polybutadiene, poly(N-vinylcarbazole), hydrocarbonresin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinylacetate, ABS resin, polyurethane, melamine resin, unsaturated polyesterresin, alkyd resin, epoxy resin and silicone resin.

[0076] The material for the electron-injecting layer andelectron-transporting layer may be any as long as it has any one of afunction of injecting electrons from the cathode, a function oftransporting electrons and a function of blocking holes injected fromthe anode. Specific examples thereof include various metal complexesincluding metal complexes of triazole derivative, oxazole derivative,oxadiazole derivative, fluorenone derivative, anthraquinodimethanederivative, anthrone derivative, diphenylquinone derivative, thiopyrandioxide derivative, carbodiimide derivative, fluorenylidenemethanederivative, distyrylpyrazine derivative, heterocyclic tetracarboxylicacid anhydrides (e.g., naphthalene perylene), phthalocyanine derivativeand 8-quinolinol derivative, and metal complex containing metalphthalocyanine, benzoxazole or benzothiazole as a ligand. Theelectron-injecting layer and the electron-transporting layer are notparticularly limited on the thickness, however, the thickness is usuallyin the range of preferably from 1 nm to 5 μm, more preferably from 5 nmto 1 μm, still more preferably from 10 to 500 nm. The electron-injectinglayer and the electron-transporting layer each may have a single layerstructure comprising one or more of the above-described materials or mayhave a multi-layer structure comprising a plurality of layers which arethe same or different in the composition.

[0077] The electron-injecting layer and the electron-transporting layereach is formed by a vacuum evaporation method, an LB method, an inkjetmethod, a method of dissolving or dispersing the above-describedelectron-injecting and transporting agent in a solvent and coating thesolution or dispersion (e.g., spin coating, casting, dip coating) or aprinting method. In the case of the coating method, the material can bedissolved or dispersed together with a resin component. Examples of theresin component include those described for the hole-injecting andtransporting layer.

[0078] The material for the protective layer may be any as long as ithas a function of preventing a substance which accelerates deteriorationof the device, such as moisture and oxygen, from entering the device.Specific examples thereof include metals such as In, Sn, Pb, Au, Cu, Ag,Al, Ti and Ni, metal oxides such as MgO, SiO, SiO₂, Al₂O₃, GeO, NiO,CaO, BaO, Fe₂O₃, Y₂O₃ and TiO₂, metal fluorides such as MgF₂, LiF, AlF₃and CaF₂, polyethylene, polypropylene, polymethyl methacrylate,polyimide, polyurea, polytetrafluoroethylene,polychlorotrifluoroethylene, polydichlorodifluoroethylene, a copolymerof chlorotrifluoroethylene and dichlorodifluoroethylene, a copolymerobtained by copolymerizing a monomer mixture containingtetrafluoroethylene and at least one comonomer, a fluorine-containingcopolymer having a cyclic structure in the copolymer main chain, a waterabsorptive substance having a coefficient of water absorption of 1% ormore, and a moisture-proofing substance having a coefficient of waterabsorption of 0.1% or less.

[0079] The method for forming the protective layer is not particularlylimited and, for example, a vacuum evaporation method, a sputteringmethod, a reactive sputtering method, an MBE (molecular beam epitaxy)method, a cluster ion beam method, an ion plating method, a plasmapolymerization method (high frequency exciting ion plating method), aplasma CVD method, a laser CVD method, a thermal CVD method, a gassource CVD method, a coating method, an inkjet method and a printingmethod may be used.

[0080] Preferred embodiments of the present invention are describedbelow.

[0081] 1) A compound represented by the following formula (I):

[0082] wherein R₁ to R₇ each independently represents hydrogen atom, ahalogen atom, a cyano group, a formyl group, a substituted orunsubstituted alkyl group, a substituted or unsubstituted alkenyl group,a substituted or unsubstituted alkynyl group, a substituted orunsubstituted aryl group, a substituted or unsubstituted heterocyclicgroup, a substituted or unsubstituted primary amino group, a substitutedor unsubstituted secondary amino group, a substituted or unsubstitutedtertiary amino group, a substituted or unsubstituted imino group, asubstituted or unsubstituted alkoxy group, a substituted orunsubstituted aryloxy group, a substituted or unsubstituted alkylthiogroup, a substituted or unsubstituted arylthio group, a substituted orunsubstituted carbonamido group, a substituted or unsubstitutedsulfonamido group, a substituted or unsubstituted carbamoyl group, asubstituted or unsubstituted sulfamoyl group, a substituted orunsubstituted alkylcarbonyl group, a substituted or unsubstitutedarylcarbonyl group, a substituted or unsubstituted alkylsulfonyl group,a substituted or unsubstituted arylsulfonyl group, a substituted orunsubstituted alkoxycarbonyl group, a substituted or unsubstitutedaryloxycarbonyl group, a substituted or unsubstituted alkylcarbonyloxygroup, a substituted or unsubstituted arylcarbonyloxy group, asubstituted or unsubstituted urethane group, a substituted orunsubstituted ureido group or a substituted or unsubstituted carboxylicacid ester group, two or more groups selected from R₁ to R₇ may combinewith each other to form an aliphatic carbon ring, an aromatic carbonring, a non-aromatic heterocyclic ring or an aromatic heterocyclic ring,and a polymer compound having the structure represented by formula (I)in a part of the repeating unit thereof may also be formed.

[0083] 2) An organic light-emitting device material comprising at leastone compound represented by formula (I) or a precursor thereof.

[0084] 3) The organic light-emitting device material as described inEmbodiment 1 or 2, which contains a polymer compound derived from acompound containing a polymerizable group in R₁ to R₇ in formula (I).

[0085] 4) An organic light-emitting device comprising at least oneorganic light-emitting device material described in Embodiments 1 to 3.

[0086] 5) The organic light-emitting device as described in Embodiment4, wherein at least one organic layer is formed by coating.

[0087] 6) A compound wherein in formula (II) or (III), R is hydrogenatom.

[0088] 7) A compound wherein in formula (II) or (III), at least one ofR₁₁ to R₁₄ has a substituent except for hydrogen atom.

[0089] 8) A compound wherein in formula (II) or (III), at least one ofR₁₁ to R₁₄ has a substituent except for hydrogen atom and being selectedfrom the group consisting of an alkyl group, an aryl group, an alkenylgroup, an alkynyl group and a heterocyclic group.

[0090] 9) A compound wherein in formula (II) or (III), at least one ofR₁₅ and R₁₆ has two or more benzene rings or at least one substituentselected from a condensed polycycloaromatic hydrocarbon group and aheteroaromacyclic group.

[0091] 10) An organic light-emitting device material comprising at leastone compound represented by formula (II) or (III).

[0092] 11) An organic light-emitting device comprising at least oneorganic light-emitting device material comprising at least one compoundrepresented by formula (II) or (III).

[0093] 12) An organic light-emitting device comprising at least onehole-transporting layer between a pair of electrodes, wherein thehole-transporting layer contains at least one compound represented byformula (II) or (III).

[0094] 13) An organic light-emitting device comprising at least onehole-injecting layer between a pair of electrodes, wherein thehole-injecting layer contains at least one compound represented byformula (II) or (III).

[0095] 14) An organic light-emitting device comprising at least oneelectron-transporting layer between a pair of electrodes, wherein theelectron-transporting layer contains at least one compound representedby formula (II) or (III).

[0096] 15) An organic light-emitting device comprising at least oneelectron-injecting layer between a pair of electrodes, wherein theelectron-injecting layer contains at least one compound represented byformula (II) or (III).

[0097] 16) An organic light-emitting device comprising at least onelight-emitting layer between a pair of electrodes, wherein thelight-emitting layer contains at least one compound represented byformula (II) or (III).

[0098] 17) The organic light-emitting device as described in Embodiments11) to 16) , wherein at least one organic layer is formed by coating.

[0099] 18) An organic light-emitting device material comprising at leastone compound represented by formula (V).

[0100] 19) An organic light-emitting device comprising at least oneorganic light-emitting device material comprising at least one compoundrepresented by formula (V).

[0101] 20) An organic light-emitting device comprising at least onehole-transporting layer between a pair of electrodes, wherein thehole-transporting layer contains at least one compound represented byformula (V).

[0102] 21) An organic light-emitting device comprising at least onehole-injecting layer between a pair of electrodes, wherein thehole-injecting layer contains at least one compound represented byformula (V).

[0103] 22) An organic light-emitting device comprising at least oneelectron-transporting layer between a pair of electrodes, wherein theelectron-transporting layer contains at least one compound representedby formula (V).

[0104] 23) An organic light-emitting device comprising at least oneelectron-injecting layer between a pair of electrodes, wherein theelectron-injecting layer contains at least one compound represented byformula (V).

[0105] 24) An organic light-emitting device comprising at least onelight-emitting layer between a pair of electrodes, wherein thelight-emitting layer contains at least one compound represented byformula (V).

[0106] 25) The organic light-emitting device as described in Embodiments19) to 24), wherein at least one organic layer is formed by coating.

[0107] The present invention is described in greater detail below byreferring to the Examples, however, the present invention should not beconstrued as being limited thereto.

EXAMPLE 1

[0108] A glass plate of 25 mm×25 mm×0.7 mm having formed thereon an ITOfilm to a thickness of 150 nm (produced by Tokyo Sanyo Shinku K.K.) wasused as a transparent support plate. This transparent support plate wasetched and washed and thereafter, copper phthlocyanine was depositedthereon to about 10 nm. Subsequently, TPD(N,N′-bis(3-methylphenyl)-N,N′-diphenylbenzidine) and Alq(tris(8-hydroxyquinolinato)aluminum) as the third layer weresequentially deposited to about 40 nm and about 60 nm, respectively, invacuum under the conditions that the plate temperature was roomtemperature. On the thus-formed organic thin film, a patterned mask (amask of giving an emission area of 5 mm×5 mm) was placed and in anevaporation unit, magnesium:silver (10:1) were co-deposited to 250 nmand then silver was deposited to 300 nm to manufacture Device 101.

[0109] EL Devices 102 to 108 having the same composition as Device 101were manufactured except for using three kinds of Comparative Compoundsand four kinds of compounds of the present invention in place of TPD ofDevice 101.

[0110] A d.c. constant voltage was applied to the EL device using SourceMeasure Unit Model 2400 manufactured by Toyo Technica and light wasemitted. The luminance and the emission wavelength were measured byLuminance Meter BM-8 manufactured by Topcon KK and Spectrum AnalyzerPMA-11 manufactured by Hamamatsu Photonics KK, respectively. The resultsare shown in Table 1 below. TABLE 1 Hole- Luminance at AppliedTransporting Emission Voltage of 10 V Device No. Material λmax (nm)(cd/m²) 101 (Comparative TPD 525 5500 Example) 102 (Comparative A 521153 Example) 103 (Comparative B 525 257 Example) 104 (Comparative C 524275 Example) 105 (Invention) A-HT-16 527 5600 106 (Invention) A-HT-19526 6020 107 (Invention) A-HT-22 525 7500 108 (Invention) A-HT-28 5237100

[0111]

[0112] Each device was sealed in an autoclave purged with argon gas andafter storage for 10 days under the heating condition of 85° C., themeasurement of luminance and the observation of emission plane statewere performed in the same manner. The results are shown in Table 2below. TABLE 2 Emission Plane Luminance at State Emission AppliedVoltage of (evaluation Device No. λmax (nm) 10 V (cd/m²) with an eye)101 (Comparative 523 1470 Poor Example) 102 (Comparative 522 35 PoorExample) 103 (Comparative 524 107 Poor Example) 104 (Comparative 525 103Poor Example) 105 (Invention) 526 2600 Fair 106 (Invention) 527 5300Good 107 (Invention) 525 6500 Good 108 (Invention) 524 6600 Good

[0113] As is apparent from the results in Table 1, light emitted fromDevices 102 to 104 fabricated using a comparative compound was low inthe luminance as compared with Device 101 as a type. On the other hand,in Devices 105 to 108 fabricated using the hole-transporting material ofthe present invention, light emission equal to or greater than that ofthe type was observed.

[0114] Furthermore, as seen from the results in Table 2, in the devicesusing the compound of the present invention, the durability was alsosuperior to the performance of the type.

EXAMPLE 2

[0115] On an ITO glass plate which was etched and washed in the samemanner as in Example 1, a solution having dissolved therein 40 mg ofpoly(N-vinylcarbazole) (PVK), 12 mg of2,5-bis(1-naphthyl)-1,3,4-oxadiazole, 10 mg of coumarin-6 and 3 ml of1,2-dichloroethane was spin-coated. At this time, the thickness of theorganic layer was about 120 nm. Subsequently, the cathode was depositedin the same manner as in Example 1 to manufacture EL Device 201.

[0116] EL Devices 202 to 205 having the same composition as Device 201were manufactured except for using two kinds of Comparative Compoundsand two kinds of compounds of the present invention in place of PVK ofDevice 201.

[0117] A d.c. constant voltage was applied to the EL device using SourceMeasure Unit Model 2400 manufactured by Toyo Technica and light wasemitted. The luminance and the emission wavelength were measured byLuminance Meter BM-8 manufactured by Topcon KK and Spectrum AnalyzerPMA-11 manufactured by Hamamatsu Photonics KK, respectively. The resultsare shown in Table 3 below. TABLE 3 Hole- Luminance at TransportingEmission Applied Voltage Device No. Material λmax (nm) of 18 V (cd/m²)201 (Comparative PVK 518 2000 Example) 202 (Comparative D 521 1720Example) 203 (Comparative E 517 1530 Example) 204 (Invention) A-HT-32520 4000 205 (Invention) A-HT-34 519 3800

[0118]

[0119] As is apparent from the results in Table 3, light emitted fromDevices 202 and 203 fabricated using a comparative compound was low inthe luminance as compared with Device 201 as a type. On the other hand,in Devices 204 and 205 fabricated using the hole-transporting materialof the present invention, light emission equal to or greater than thatof the type was observed.

EXAMPLE 3

[0120] EL Devices 302 to 310 having the same composition as Device 101were manufactured except for using three kinds of Comparative Compoundsand four kinds of compounds of the present invention in place of TPD ofDevice 101 in Example 1.

[0121] A d.c. constant voltage was applied to the EL device using SourceMeasure Unit Model 2400 manufactured by Toyo Technica and light wasemitted. The luminance and the emission wavelength were measured byLuminance Meter BM-8 manufactured by Topcon KK and Spectrum AnalyzerPMA-11 manufactured by Hamamatsu Photonics KK, respectively. The resultsare shown in Table 4 below. TABLE 4 Hole- Luminance at TransportingEmission Applied Voltage Device No. Material λmax (nm) of 10 V (cd/m²)101 (Comparative TPD 525 5500 Example) 302 (Comparative F 524 5200Example) 303 (Comparative G 523 5350 Example) 304 (Comparative H 5245550 Example) 305 (Invention) B-HT-1 526 5600 306 (Invention) B-HT-3 5255650 307 (Invention) B-HT-5 524 5450 308 (Invention) B-HT-6 525 5450 309(Invention) B-HT-10 524 5500 310 (Invention) B-HT-15 525 5600

[0122]

[0123] Each device was sealed in an autoclave purged with argon gas andafter storage for 10 days under the heating condition of 85° C., themeasurement of luminance and the observation of emission plane statewere performed in the same manner. The results are shown in Table 5below. TABLE 5 Luminance at Emission Plate Emission Applied VoltageState (evaluation Device No. λmax (nm) of 10 V (cd/m²) with an eye) 101(Comparative 523 1470 Poor Example) 302 (Comparative 524 350 PoorExample) 303 (Comparative 523 200 Poor Example) 304 (Comparative 524 325Poor Example) 305 (Invention) 525 5300 Good 306 (Invention) 525 5400Good 307 (Invention) 524 5250 Good 308 (Invention) 525 5200 Good 309(Invention) 526 5300 Good 310 (Invention) 525 5450 Good

[0124] On comparison between the results in Table 4 and the results inTable 5, light emission observed immediately after the fabrication isequal to that of the type in all devices. On the other hand, comparisonon the device performance after high-temperature aging clearly revealsthat Devices 305 to 310 using the compound of the present invention aresuperior in the durability to the type.

EXAMPLE 4

[0125] On an ITO glass plate which was etched and washed in the samemanner as in Example 1, a solution having dissolved therein 30 mg ofpolycarbonate, 30 mg of TPD and 3 ml of 1,2-dichloroethane wasspin-coated. At this time, the thickness of the organic layer was about60 nm. Subsequently, Alq and cathode were deposited in the same manneras in Example 1 to manufacture EL Device 401.

[0126] EL Devices 402 to 405 having the same composition as Device 401were manufactured except for using two kinds of Comparative Compoundsand two kinds of compounds of the present invention in place of TPD ofDevice 401.

[0127] A d.c. constant voltage was applied to the EL device using SourceMeasure Unit Model 2400 manufactured by Toyo Technica and light wasemitted. The luminance and the emission wavelength were measured byLuminance Meter BM-8 manufactured by Topcon KK and Spectrum AnalyzerPMA-11 manufactured by Hamamatsu Photonics KK, respectively. The resultsare shown in Table 6 below. TABLE 6 Hole- Luminance at TransportingEmission Applied Voltage Device No. Material λmax (nm) of 18 V (cd/m²)401 (Comparative TPD 522 2550 Example) 402 (Comparative F 521 2550Example) 403 (Comparative H 522 2600 Example) 404 (Invention) B-HT-1 5212650 405 (Invention) B-FT-10 521 2600

[0128] Each device was sealed in an autoclave purged with argon gas andafter storage for 10 days under the heating condition of 85° C., themeasurement of luminance and the observation of emission plane statewere performed in the same manner. The results are shown in Table 7below. TABLE 7 Luminance at Emission Plate Emission Applied VoltageState (evaluation Device No. λmax (nm) of 18 V (cd/m²) with an eye) 401(Comparative 521 200 Poor Example) 402 (Comparative 522 210 PoorExample) 403 (Comparative 522 190 Poor Example) 404 (Invention) 521 2350Good 405 (Invention) 521 2400 Good

[0129] In the results shown in Table 6, luminance of all devices isequal to that of Device 401, however, from the results shown in Table 7,it is seen that Devices 404 to 405 using the compound of the presentinvention are superior in the durability during storage underhigh-temperature conditions to Comparative Devices 401 to 403. Theseresults reveal that the compounds of the present invention are effectiveas compared with the comparative compounds.

EXAMPLE 5 (Synthesis of Compound INB-1)

[0130] Through a solution obtained by dissolving 959 mg (5 mmol) of2-phenylindolizine and 3.75 ml of tetramethylethylenediamine (TMEDA) in50 ml of waterless tetrahydrofuran (THF) for organic synthesischemistry, a nitrogen stream was passed and while stirring, the innertemperature was kept at −40° C. or less using a dry ice bath. Thereto,3.41 ml (5.5 mmol) of a 1.6N n-butyllithiumhexane solution was addeddropwise while taking care not to allow the inner temperature to exceed−40° C. After the completion of dropwise addition, stirring wascontinued for 3 hours under the same temperature condition. To theresulting reaction mixture, 1,395 mg (7.5 mmol) of2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane was added dropwiseand stirring was continued at that temperature for 2 hours. Thereafter,the dry ice bath was removed and the stirring was further continueduntil the condition reached room temperature. The reaction mixture waspoured into ether/aqueous 0.1N ammonium chloride solution and subjectedto a liquid separation operation. Thereafter, the ether phase wasfurther subjected to a liquid separation operation with water. Afterremoving the aqueous phase, the ether phase was dried over anhydroussodium sulfate and the solvent was distilled off under reduced pressure.To the oily compound obtained, acetonitrile was added and the mixturewas heated and then cooled, as a result, crystals were precipitated. Thecrystals were separated by filtration and dried to obtain 1,022 mg ofcrystals of INB-1.

(Synthesis of Compound C-HT-10)

[0131] In 20 ml of diethylene glycol dimethyl ether, 3.02 g (10 mmol) ofCompound INB-1 and 944 mg (3 mmol) of 1,3,5-tribromobenzene weredissolved and thereto, 1 ml of water, 2.12 g (20 mmol) of sodiumcarbonate, a catalytic amount of Pd—Carbon (Pd: 5%) andtriphenylphosphine were added and refluxed for 5 hours. With theprogress of reaction, the product was produced as crystals. After thereaction, the reaction mixed solution was added to a chloroform/watermixed solvent and after thorough stirring, the solution was filteredthrough Celite. The chloroform phase of the filtrate wasliquid-separated and further liquid-separated with water. Thereafter,the chloroform phase was dried over anhydrous sodium sulfate and thesolvent was distilled off under reduced pressure. The crystals obtainedwere recrystallized from a THF-methanol mixed solvent to obtain 2.7 g ofcrystals of Compound C-HT-10.

(Evaluation 1 as Organic Light-Emitting Device Material)

[0132] EL Devices 502 to 508 having the same composition as Device 101were manufactured except for using seven kinds of compounds of thepresent invention in place of TPD of Device 101 in Example 1.

[0133] A d.c. constant voltage was applied to the EL device using SourceMeasure Unit Model 2400 manufactured by Toyo Technica and light wasemitted. The luminance and the emission wavelength were measured byLuminance Meter BM-8 manufactured by Topcon KK and Spectrum AnalyzerPMA-11 manufactured by Hamamatsu Photonics KK, respectively. The resultsare shown in Table 8 below. TABLE 8 Hole- Luminance at TransportingEmission Applied Voltage Device No. Material λmax (nm) of 10 V (cd/m²)101 (Comparative TPD 525 5500 Example) 502 (Invention) C-HT-1 523 5600503 (Invention) C-HT-3 525 5550 504 (Invention) C-HT-6 525 5550 505(Invention) C-HT-8 524 5450 506 (Invention) C-HT-10 526 5400 507(Invention) C-HT-15 525 5350 508 (Invention) C-HT-19 524 5600

[0134] As is apparent from the results in Table 8, in Devices 502 to 508using the compound of the present invention, light emission equal tothat of the type was also observed.

Evaluation 2 as Organic Light-Emitting Device Material)

[0135] EL Devices 602 to 605 having the same composition as Device 401were manufactured except for using four kinds of compounds of thepresent invention in place of TPD of Device 401 in Example 4.

[0136] A d.c. constant voltage was applied to the EL device using SourceMeasure Unit Model 2400 manufactured by Toyo Technica and light wasemitted. The luminance and the emission wavelength were measured byLuminance Meter BM-8 manufactured by Topcon KK and Spectrum AnalyzerPMA-11 manufactured by Hamamatsu Photonics KK, respectively. The resultsare shown in Table 9 below. TABLE 9 Hole- Luminance at TransportingEmission Applied Voltage Device No. Material λmax (nm) of 10 V (cd/m²)401 (Comparative TPD 522 2550 Example) 602 (Invention) C-HT-1 521 2400503 (Invention) C-HT-6 522 2500 604 (Invention) C-HT-8 522 2500 605(Invention) C-HT-15 521 2450

[0137] As is apparent from the results in Table 9, in Devices 602 to 605using the compound of the present invention, light emission equal tothat of the type was also observed.

[0138] By using the indolizine compound of the present invention, alight-emitting device favored with high luminance, excellent durabilityin the storage under high-temperature conditions and good emission planestate can be obtained.

[0139] Furthermore, by using the 5-substituted indolizine compound ofthe present invention, an organic light-emitting device ensuring highluminance can be obtained.

[0140] While the invention has been described in detail and withreference to specific embodiments thereof, it will be apparent to oneskilled in the art that various changes and modifications can be madetherein without departing from the spirit and scope thereof.

What is claimed is:
 1. An organic light-emitting device materialcomprising at least one compound represented by formula (I) or aprecursor thereof:

wherein R₁ to R₇ each independently represents hydrogen atom, a halogenatom, a cyano group, a formyl group, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted alkenyl group, a substitutedor unsubstituted alkynyl group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted heterocyclic group, a substitutedor unsubstituted primary amino group, a substituted or unsubstitutedsecondary amino group, a substituted or unsubstituted tertiary aminogroup, a substituted or unsubstituted imino group, a substituted orunsubstituted alkoxy group, a substituted or unsubstituted aryloxygroup, a substituted or unsubstituted alkylthio group, a substituted orunsubstituted arylthio group, a substituted or unsubstituted carbonamidogroup, a substituted or unsubstituted sulfonamido group, a substitutedor unsubstituted carbamoyl group, a substituted or unsubstitutedsulfamoyl group, a substituted or unsubstituted alkylcarbonyl group, asubstituted or unsubstituted arylcarbonyl group, a substituted orunsubstituted alkyl-sulfonyl group, a substituted or unsubstitutedarylsulfonyl group, a substituted or unsubstituted alkoxycarbonyl group,a substituted or unsubstituted aryloxycarbonyl group, a substituted orunsubstituted alkylcarbonyloxy group, a substituted or unsubstitutedarylcarbonyloxy group, a substituted or unsubstituted urethane group, asubstituted or unsubstituted ureido group or a substituted orunsubstituted carboxylic acid ester group, two or more groups selectedfrom R₁ to R₇ may combine with each other to form an aliphatic carbonring, an aromatic carbon ring, a non-aromatic heterocyclic ring or anaromatic heterocyclic ring and R₄ may further represent

R₈ and R₉ each represents hydrogen atom, an alkyl group, an aryl groupor a heterocyclic group, R₈ and R₉ may combine with each other to form acyclic structure or may form a polymer compound having the structurerepresented by formula (I) in a part of the repeating unit thereof andR₁ or R₃ in the structure represented by formula (I) and

may combine to form a trimer compound, and R represents hydrogen atom,an alkyl group, an aryl group or a heterocyclic group.
 2. The organiclight-emitting device material as claimed in claim 1 , which contains apolymer compound derived from a compound containing a polymerizablegroup in R₁ to R₇ of formula (I) , a trimer compound formed resultingfrom the combining of R₁ or R₃ in formula (I) and

or a compound in which R₄ in formula (I) is


3. A compound represented by the following formula

wherein R₂₁ to R₂₆ each independently represents a substituent selectedfrom the group consisting of hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted alkenyl group,a substituted or unsubstituted alkynyl group, a substituted orunsubstituted aryl group, a substituted or unsubstituted heterocyclicgroup, a substituted or unsubstituted alkoxy group, a substituted orunsubstituted aryloxy group, a substituted or unsubstituted alkylthiogroup, a substituted or unsubstituted arylthio group, a substituted orunsubstituted alkylamino group, a substituted or unsubstituted arylaminogroup, a substituted or unsubstituted alkylcarbonyl group, a substitutedor unsubstituted arylcarbonyl group, a substituted or unsubstitutedalkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group,a substituted or unsubstituted alkoxycarbonyl group, a substituted orunsubstituted aryloxycarbonyl group, a substituted or unsubstitutedalkylcarbamoyl group, a substituted or unsubstituted arylcarbamoylgroup, a substituted or unsubstituted alkylsulfamoyl group, asubstituted or unsubstituted arylsulfamoyl group, a substituted orunsubstituted alkylcarbonyloxy group, a substituted or unsubstitutedarylcarbonyloxy group, a substituted or unsubstituted alkylcarbonamidogroup, a substituted or unsubstituted arylcarbonamido group, asubstituted or unsubstituted alkylsulfonamido group, a substituted orunsubstituted arylsulfonamido group, a substituted or unsubstitutedurethane group, a substituted or unsubstituted ureido group and asubstituted or unsubstituted carbonic acid ester group, the substituentsselected from R₂₁ to R₂₆ may combine with each other to form a cyclicstructure, R₂₇ and R₂₈ each represents hydrogen atom, an alkyl group, anaryl group or a heterocyclic group, and R₂₇ and R₂₈ may combine witheach other to form a cyclic structure.
 4. A method for synthesizing acompound represented by the following formula (IV), comprisingmetalating an indolizine derivative not having a substituent at the5-position and then reacting it with a boric acid ester compound:

wherein R₂₁ to R₂₆ each independently represents a substituent selectedfrom the group consisting of hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted alkenyl group,a substituted or unsubstituted alkynyl group, a substituted orunsubstituted aryl group, a substituted or unsubstituted heterocyclicgroup, a substituted or unsubstituted alkoxy group, a substituted orunsubstituted aryloxy group, a substituted or unsubstituted alkylthiogroup, a substituted or unsubstituted arylthio group, a substituted orunsubstituted alkylamino group, a substituted or unsubstituted arylaminogroup, a substituted or unsubstituted alkylcarbonyl group, a substitutedor unsubstituted arylcarbonyl group, a substituted or unsubstitutedalkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group,a substituted or unsubstituted alkoxycarbonyl group, a substituted orunsubstituted aryloxycarbonyl group, a substituted or unsubstitutedalkylcarbamoyl group, a substituted or unsubstituted arylcarbamoylgroup, a substituted or unsubstituted alkylsulfamoyl group, asubstituted or unsubstituted arylsulfamoyl group, a substituted orunsubstituted alkylcarbonyloxy group, a substituted or unsubstitutedarylcarbonyloxy group, a substituted or unsubstituted alkylcarbonamidogroup, a substituted or unsubstituted arylcarbonamido group, asubstituted or unsubstituted alkylsulfonamido group, a substituted orunsubstituted arylsulfonamido group, a substituted or unsubstitutedurethane group, a substituted or unsubstituted ureido group and asubstituted or unsubstituted carbonic acid ester group, the substituentsselected from R₂₁ to R₂₆ may combine with each other to form a cyclicstructure, R₂₇ and R₂₈ each represents hydrogen atom, an alkyl group, anaryl group or a heterocyclic group, and R₂₇ and R₂₈ may combine witheach other to form a cyclic structure.
 5. A method for producing acompound represented by the following formula (V), comprising coupling acompound represented by the following formula (IV) with a vinyl halide,aryl halide or heteroaryl halide compound using a palladium catalyst:

wherein R₂₁ to R₂₆ each independently represents a substituent selectedfrom the group consisting of hydrogen atom, a substituted orunsubstituted alkyl group, a substituted or unsubstituted alkenyl group,a substituted or unsubstituted alkynyl group, a substituted orunsubstituted aryl group, a substituted or unsubstituted heterocyclicgroup, a substituted or unsubstituted alkoxy group, a substituted orunsubstituted aryloxy group, a substituted or unsubstituted alkylthiogroup, a substituted or unsubstituted arylthio group, a substituted orunsubstituted alkylamino group, a substituted or unsubstituted arylaminogroup, a substituted or unsubstituted alkylcarbonyl group, a substitutedor unsubstituted arylcarbonyl group, a substituted or unsubstitutedalkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group,a substituted or unsubstituted alkoxycarbonyl group, a substituted orunsubstituted aryloxycarbonyl group, a substituted or unsubstitutedalkylcarbamoyl group, a substituted or unsubstituted arylcarbamoylgroup, a substituted or unsubstituted alkylsulfamoyl group, asubstituted or unsubstituted arylsulfamoyl group, a substituted orunsubstituted alkylcarbonyloxy group, a substituted or unsubstitutedarylcarbonyloxy group, a substituted or unsubstituted alkylcarbonamidogroup, a substituted or unsubstituted arylcarbonamido group, asubstituted or unsubstituted alkylsulfonamido group, a substituted orunsubstituted arylsulfonamido group, a substituted or unsubstitutedurethane group, a substituted or unsubstituted ureido group and asubstituted or unsubstituted carbonic acid ester group, the substituentsselected from R₂₁ to R₂₆ may combine with each other to form a cyclicstructure, R₂₇ and R₂₈ each represents hydrogen atom, an alkyl group, anaryl group or a heterocyclic group, and R₂₇ and R₂₈ may combine witheach other to form a cyclic structure,

wherein R₂₀ represents an alkenyl group, an aryl group or a heteroarylgroup, and R₂₁ to R₂₆ are the same as the substituent described informula (IV).
 6. An organic light-emitting device having at least oneorganic light-emitting device material comprising at least one compoundrepresented by formula (I) or a precursor thereof:

wherein R₁ to R₇ each independently represents hydrogen atom, a halogenatom, a cyano group, a formyl group, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted alkenyl group, a substitutedor unsubstituted alkynyl group, a substituted or unsubstituted arylgroup, a substituted or unsubstituted heterocyclic group, a substitutedor unsubstituted primary amino group, a substituted or unsubstitutedsecondary amino group, a substituted or unsubstituted tertiary aminogroup, a substituted or unsubstituted imino group, a substituted orunsubstituted alkoxy group, a substituted or unsubstituted aryloxygroup, a substituted or unsubstituted alkylthio group, a substituted orunsubstituted arylthio group, a substituted or unsubstituted carbonamidogroup, a substituted or unsubstituted sulfonamido group, a substitutedor unsubstituted carbamoyl group, a substituted or unsubstitutedsulfamoyl group, a substituted or unsubstituted alkylcarbonyl group, asubstituted or unsubstituted arylcarbonyl group, a substituted orunsubstituted alkylsulfonyl group, a substituted or unsubstitutedarylsulfonyl group, a substituted or unsubstituted alkoxycarbonyl group,a substituted or unsubstituted aryloxycarbonyl group, a substituted orunsubstituted alkylcarbonyloxy group, a substituted or unsubstitutedarylcarbonyloxy group, a substituted or unsubstituted urethane group, asubstituted or unsubstituted ureido group or a substituted orunsubstituted carboxylic acid ester group, two or more groups selectedfrom R₁ to R₇ may combine with each other to form an aliphatic carbonring, an aromatic carbon ring, a non-aromatic heterocyclic ring or anaromatic heterocyclic ring and R₄ may further represent

R₈ and R₉ each represents hydrogen atom, an alkyl group, an aryl groupor a heterocyclic group, R₈ and R₉ may combine with each other to form acyclic structure or may form a polymer compound having the structurerepresented by formula (I) in a part of the repeating unit thereof andR₁ or R₃ in the structure represented by formula (I) and

may combine to form a trimer compound, and R represents hydrogen atom,an alkyl group, an aryl group or a heterocyclic group.
 7. The organiclight-emitting device as claimed in claim 6 , wherein at least oneorganic layer is formed by coating.